Sightseeing:

Willis (Sears) Tower

John Hancock

Shedd Aquarium

Chicago Art Institute

The Bean/Millennium Park

Buckingham Fountain

Adler Planetarium (great city skyline view)

Michigan Ave/Magnificent Mile (shopping)

Chinatown

Art Institute of Chicago

Field Museum

Downtown Riverwalk

Garfield Park Conservatory

Wendella boat tour (architectural, sunset)

For the kids:

Brookfield Zoo

Lincoln Park Zoo

LegoLand (Woodfield Mall, Schaumburg)

Museum of Science and Industry

Breweries/Pubs:

Goose Island Brewery (Chicago)

Guiness (Chicago)

Lagunitas Brewing Co (Chicago)

Imperial Oak Brewery (Willow Springs)

Noon Whistle Brewery (Lombard)

Alter Brewing Co (Oak Brook)

Restaurants/Bars:

Brunch:

Honey Jam Cafe (multiple locations)

Egg Harbor Cafe (multiple locations)

Lumes - Willowbrook & Orland Park

Darlene's - Orland Park

Lunch & Dinner:

Portillo's (Chicago must-try)

Lou Malnati's Deep Dish Pizza

Giordano's Deep Dish Pizza

Capri - Burr Ridge

Beatrix - Oak Brook

Blanco Cocina + Cantina - Oak Brook

Fat Rosie's - Oak Brook & Schaumburg

Labriola - Oak Brook

Dell Rhea's Chicken Basket - Willowbrook

Subamma's Kitchen - Aurora

Priya's Kitchen - Orland Park

Vanam - (vegetarian) Schaumburg

Desi Chowrasthra - Naperville

Beatnik - Ukrainian Village

Cerise Rooftop - downtown

Celeste - North Riverside

Cindy's Rooftop - downtown

Velvet Taco - Naperville, Chicago

Quartino - Magnificent Mile

Summer House Santa Monica - Lincoln Park

Firecakes Donuts - Chicago

Damascus Cafe - Willowbrook

Coffee/Chai:

Qahwah House

Qamaria

Shaghf Cafe

Folklore Cafe - Lemont

Arcadia Coffee - Downers Grove

Speakeasy (Chicago):

Bordel

The Drifter

Scofflaw

Green Mill Jazz Club

The Library/Gilt Bar

Storyville

Shopping:

Fashion Outlets in Rosemont

Chicago Premium Outlets in Aurora

Oak Brook Mall

York Town Mall (Lombard)